Saturday Night
by Selim
Summary: Toothless has a problem - a big one. About to enter his last year of school, it occurs to him he's the only virgin in his class. In hopes to rectify that, he stumbled upon a number for a prostitute. One night is never so easy. ToothlessSlut?Hiccup
1. Chapter 1

Saturday Night  
By: Selim  
Rating: M+  
Summary: Toothless has a problem - a big one. About to enter his last year of school, it occurs to him he's the only virgin in his class. In hopes to rectify that, he stumbled upon a number for a prostitute. One night is never so easy.  
Pairings: Human-Toothless/slut?Hiccup  
Warnings: Language, situations, and themes.

Disclaimer: I do not own How to Train Your Dragon. This is a piece of fiction and the author is making no monetary gain off its creation.

Additional notes: Yes, I have 2 other fics to write. I'm hoping to wean myself back into writing by starting a new story. Work with me on this, it took a year but I finally only have 1 report left to write for work so I can start fanfiction writing again. Anyway, once upon a time Loti-Miko asked if I would ever do a High School fic. At the time, I said no because I haven't been in high school in... years and the rules have changed and vary by country. Well, I did one.

Berk is a high-bred of multiple countries education system. At 15 students apply to attend what's called "college" or a high school. It has 3 years that focus on career planning before students move on to University of their choices. Not everyone attending Berk Academy (The Private School) will make it to third year. The school selects only 100 students of each year to attend the final year. Those who don't make it move back to the public school.

* * *

_That is one sexy man._

Running his comb through his hair one last time to give the spikes the right amount of lift, Toothless flashed a white smile at his reflection.

It was so hard to have some form of individuality at this school. As one of the more prestigious in the country, the teachers were sticklers to the rules in regulation of the correct uniform and most likely the other students would be caught even with spiked hair. Toothless, however, would get away with it. He hid in just the right shadows to be forgotten by the teaching staff. It didn't mean that he could get away with breaking every meaningless rule he reasoned as he fixed his collar one last time.

Berk Academy was known to only send out the best students to college. Its earlier years were crowded with students, hundreds that came from surrounding towns for a chance to be one of the prestigious few. By third year, when The Interviews were made, it dropped down to a select 100 students, the brightest (and richest) of minds that would be marketed off to the finest of Universities, the main one being Berk's Professional University.

Toothless had worked hard to get into the school, two years ago. Unlike a large number of his classmates, he wasn't born with money or a pedigree. His father owned a local business that had been doing fairly well the last ten years. His mother worked her tail off at the local hospital, neither of which came from anything more than a farming lifestyle themselves. The chance to become something and help his parent's financially was always in the back of his mind when he took the school entrance exam. When he made it into the high percentile of his peers, earning a full scholarship to the school, it had only meant he worked harder than his peers to stay there.

The moment he'd walked through the doors, his classmate's had smelt the poor. He was written off as the nerdy Toothless, never one to go out partying, always studying. He had to work shifts on the weekends to have spending money and skipped school holidays to save extra cash for University. They knew what he was and none of them liked him for it.

He _earned_ this placement. They had purchased it with daddy's money.

Tossing his bag over his shoulder, he moved out to the crowded halls, mindful of the jagged shoulders that pressed into his form, the shuffle of peers talking about their weekends and latest purchases. The self-esteem he built up only seconds before deflated again as he mounted the stair case leading to the second years. Two steps ahead, bag thrown over his shoulder, Snotlout chortled with laughter as his pretty girlfriend leaned heavily into his side.

Slipping past them, he moved through the wide double doors, towards the open lecture hall that was his Registration. Snotlout was already settled in his seat up front near the window, gazing out at the birds with hopeless abandonment. Settling next to his only friend, Toothless shuffled through his bag. "I hate him."

"Hm?" Meatlug craned his neck. The meaty folds of his second chin were already accumulating with sweat, Toothless noted absently. It would only be a moment before-

Coming into the classroom, Snotlout tugged his nose back and made high pitch snorting sounds at the two. With a groan, the chubbier man glanced back at the window. "Not much you can do. He's popular, you're, well, you." He tucked his hands under his chin. "We got a few more weeks until The Interviews. Maybe the school will see how much a prick he is and send him packing? Or maybe a few wrong answers and we can go somewhere else."

Toothless shielded a glance back at Snotlout.

The tall, bulky man had been the biggest bully of Berk Academy. There was no question to how he was secured entrance into the school, he'd let everyone know he had come from money since day one. Apparently he had several family members in high-end positions at Haddock Industries, including the CEO. Toothless couldn't help but feel some resentment towards the man. Even with the financial security, the boy had enough smarts to be in the upper percentile of his classes (although Toothless' scores were still better) and was blessed with athletic skill. He always had some girl on his elbow as well, not that Toothless cared.

"Just don't let him get to you," Meatlug continued absently, "He's not worth your time. Anyway, do you have the maths workbook? I totally crashed last night after watching _Dragons and Men_ and if I miss another assignment, I'll lose my car for two months."

Handing his book over, Toothless leaned on his arm and watched the students fill the classroom. Each one in a group of his or her own, no one paying mind to the two outcasts in the corner. So many students, Toothless noted, and none of which he was close to. It hadn't occurred to him until he grabbed his bag for school a week before that he had no friends. He'd focused so much time on his studies, even his roommate had disappeared into an unfamiliar blur of red hair.

He only had three months to fix that. He didn't want to go to his third year without friends. Hell, he didn't want to go without at least a girlfriend.

There were at least thirty girls in his Registration. Of these, at least twenty-three of the girls were dating someone else in the school; he'd observed each with significant others from the canteen to the common rooms, catching the whispers of gossip while moving through the mental list of names of potential girls.

"You going to the Wandering Oar tonight?" Meatlug asked, glancing over the rim of his glasses at the door to ensure he wouldn't be caught copying his homework. "They're having a last meeting before Spring Meet, getting some drinks, hanging with friends, then go home. Come back for final test and exams, then The Interview."

The Toothless of a week ago would have immediately declined - it wasn't his scene, filled to the brim of people he couldn't stand. The same Toothless wasn't trying to have a fresh start before Third Year. "Yeah, I'll be there." He leaned forward on his elbows, taking in the old whiteboard and the scrawl across it. There were a list of activities for end year, many of which Toothless had no opinion of.

As a Civic Engineering student, his day was filled with maths and sciences with the odd writing course thrown in. His extracurricular activity of choice was art and he was part of the Tech Club, spending the first few weeks of school working on the student tablets. The rest of the year was fixing the same devices, clearing off the viruses collected through unauthorized programs and attempted hackings.

The cheering of his classmates drew his attention back, watching them circle the three star players of the school's Rugby team. The chanting continued long enough to draw their instructor into the room, breaking the chaos with a stern shout.

It was hours later, at the Wandering Oar that Toothless felt even more out of place than he ever did at school. Dressed in his own cousin's second hand clothes, alone without his wingman, he sipped at a soda while his classmates celebrated their last few hours together. The pairings were more obvious, he noted absently at the pretty girls and handsome men that had found one another. Then there was him, a ghost in the background, forgotten.

Except...

His sights fell on one lone girl watching the groups dance, a fruity drink in her hands. Her blonde hair was pulled back into two braids, blue eyes dancing with delight. _Astrid_. She was a year younger than him, another person who had their placement bought by family. As a first year, she wasn't worried yet about The Interview. It probably wouldn't hit her until this time, next year. All of these people wouldn't be as jolly first of the month.

Draining his soda, he started across the hall. Plastering on a friendly smile, he leaned against the counter next to her. "Hey, Astrid."

Her blue eyes narrowed, taking in him and trying to place a name. When the pause lasted too longer, Toothless swallowed.

"It's Toothless, second year? I, uh, fixed your computer so you could access your social network?" It had been against regulations, but she had flirted with him earlier that year with her blouse unbuttoned and white flesh under his nose. It wasn't possible to resist when she praised his computer skills.

"Oh!" Her eyes widened with realization before the smile graced her face. "I'm still so impressed that you were able to do that, you don't realize how much of a life saver you are, Toothless." She brushed a bang from her face. "I'm sorry, I'm not really good with names."

Laughing it off, Toothless reached into his wallet, ordering her another juice. "It's fine. How has your first year at the academy been?"

"Good, good - I didn't realize how competitive the program was until recently! I'm going to have several late nights this testing season if I want to move onto the Third Year here. You're about to go into The Interview, aren't you? You nervous?" She moved on fast, placing her weight on her left side.

"Um, yeah, just a little." Toothless tucked his hands into his pocket. "Um, I wanted to know if you maybe wanted to dance, or, you know, something." The party was already spiraling out of control as a flask was passed around, knowing that this was the only night the owner of the Wandering Oar would be out, leaving his son in charge.

Glancing around the room, Astrid shifted. "Look..."

"Astrid!"

Toothless jumped as Ruffnut's voice echoed across the packed bar. She jumped over, wrapping her arms around Astrid's thin arm with a confused look at Toothless .

"What are you doing hanging with the virgin?"

"We were just having a chat about third year." Astrid straightened out from under the friendly hug, tucked hands in front of her.

"Oh," Ruffnut frowned, "Whatever. Snotlout was asking for you - I think he's got the hots for you. Don't hide in back, I heard from Stormfly that a night with Snotlout is like a night in heaven. She never came so hard until-" The girl's voice faded as she pulled Astrid away. Neither girl passed a glance behind them, not that Toothless would have noticed if they had.

_Virgin._

How had they even known? Or was it a jest?

He glanced over at Snotlout, noting how the man had glanced at him before laughing with the girls.

_Why did it matter?_

He swallowed.

Leaving the bar, he rushed towards the school dorms and to his room. His roommate was already gone, either at home or at the bar, Toothless didn't know nor did he care as he grabbed at his coat, grabbing his abandoned cell phone.

Two missed messages, both from Meatlug, explaining his absence. Apparently a better offer to go off with his girlfriend who attended Berk Public College came up and Meatlug took her up on the deal. Besides, the next message explained, it was traditional to lose one's virginity before Second Year was over and it didn't matter if Meatlug enjoyed attending the school, he wasn't one to dismiss tradition.

Dropping on his bed, Toothless let his hands drop between his knees, not able to look up even as his roommate came in and left, condoms stuffed in his pocket. _When did all this happen?_ Toothless took in the room, noting the differences between his own neatly arranged area versus his roommates stifling mess of nudie magazines and school materials. The only scantily clad image he had on his person was the latest movie poster for his favorite Elf Wars Franchise with the Elven Princess plastered with her two piece mithril set. And he only got the poster as a bonus for pre-ordering his DVD box set.

Groaning, he ducked his head lower.

New plan of action, girlfriend - or boyfriend - be damned, he needed to get laid before the testing started. No one would believe him, but at least he'd know he wasn't truly left behind.

And more so, if he had a few tryst, he could make a pretty girl like Astrid talk about his prowess to her friends. It would be the icing of his cake.

Grabbing his weekend bag, he stormed out of the dorms. Everything around him seemed different with the new sense of awareness including the tall-tale signs of students having sex. Socks on the doorjambs, the occupied sign in the bathroom. There wasn't a place, he realized as he left school grounds that students weren't taking up to spend their last moments together. _You should have seen this earlier. How many girls have left school this last year pregnant?_

_I need to get out of here._

It was a requirement that the students live on campus even though a large percentage of students lived a short distance from the school. Toothless' father's restaurant was a frequent site visited by the students, but today seemed almost empty as the teen stepped, going towards the back rooms to leave his bag in his locker. His father was in the open office, reading off his computer as the cooks moved around the kitchen automatically.

"Thought you were hanging out with the other kids today?" His father hummed absently as Toothless logged into the work system.

"Those plans fell through," Toothless grumbled, grabbing his apron.

"I was going to have Bucket do it, but since you're here could you clean up the bathrooms? The stalls need a fresh coat of paint, too. Those kids might help us stay in the black, but they have no respect to my property." The man shook his head. "Once you're done, you can help in the kitchens."

Tossing his apron back down, Toothless tossed his head back with a low groan. "Whatever." He reached for the tins of paint that had been sitting on his father's filing cabinet since the beginning of the year when the man had first mentioned painting the stalls. He shifted his tongue in his mouth, tempted to inquire about his father's opinion on the school tradition, but ended up smothering the topic.

His father had been sixteen when he knocked up Toothless' mother with their oldest daughter. He wouldn't understand his own son's problems, coming up on eighteen with his virginity still intact.

The bathrooms at the restaurant were not gross by any stretch of the words. In Toothless' opinion, they appeared to be normal toilets with an unusual number of graffiti lining the door. His father was usually good about covering up inappropriate statements himself, allowing kids to be kids by leaving their mark somewhere, but every so often the stalls began to look more like a newspaper and less like a public space.

There was the usual cluster of names, defining love in ink. Occasionally someone had drawn a penis but it was scribbled out and replaced by stick figures. Toothless' favorite ones were the motivational comments the occasional shitter left, mostly because it often caused someone else to be side and sarcastic directly underneath.

Next to the toilet paper is neat block letters was written, _You are perfect the way you are._

Under it, someone's messy scrawl wrote, "_I KNOW I'm flawless. Fuck off._"

Taking his phone out, Toothless snapped a picture of it before spreading the paint over the mess.

Each line was read before erased forever, a small cluster of entertainment designed just for him. He scowled at someone who had written a message to "The nerd in third block on BA's Advanced Calculus course." Wiping that away, Toothless stepped into the stall, shutting the door to work on the inside.

"_Looking for a good time? Just text._ It was followed by a cluster of numbers. Pretty font, relatively new as far as Toothless could remember. He dipped the paintbrush into the pail.

_Just text._

Whores, the lot of them. Having to get a date through means of the uni-sex bathroom at the local shops. Or it was a boyfriend or girlfriend angry at their past conquest. Toothless grumbled, erasing part of the message only to be stopped at the number.

Or maybe it wasn't a joke? Maybe this was his only chance, someone who just wanted to get laid and didn't care by whom? He could live with a one night shag if it meant he wouldn't be a virgin anymore. Maybe things would perk up if he didn't have this aura of never been touched?

He swallowed heavily, grasping his cellphone once more. The numbers weren't hard to type it, but his fingers felt stiff and unsure. He paused on the message portion of the message. _This is stupid._ He slammed his phone back into his pocket, white washing the number away. He wasn't going to beg for a quick fuck, that didn't feel special in the least.

Ruffnut's voice caressed his ear in repeat, ""What are you doing hanging with the virgin?"

Astrid had just walked away, almost appalled with the thought of him not knowing what to do with a girl. Him, almost ready to enter his Third Year.

He grabbed his phone again. _Looking for a good time._

If it was a joke or a mean prank from an ex-lover, he could laugh this off. He would never meet this person in real life if it was all fake.

He didn't even leave the stall when his phone vibrated back with a message. _Haddock Hotels, room 227B tomorrow at noon. 50 for some touching, 100 for mouth, 150 to rub, 250 for everything._

Blinking at the prices, Toothless licked the roof of his mouth. Were those prices right? That seemed... rather expensive, but he did have that money in his savings account and his parents did say only to use it for an emergency. Losing his virginity on short notice did seem like an emergency.

With shaky fingers he sent a message back before stuffing the cell in his pocket.

_I want everything_.


	2. Chapter 2

Saturday Night  
**By**: Selim  
**Rating**: M+  
**Summary**: Toothless has a problem – a big one. About to enter his last year of school, it occurs to him he's the only virgin in his class. In hopes to rectify that, he stumbled upon a number for a prostitute. One night is never so easy.  
**Pairing**: Human-Toothless/Slut?Hiccup  
**Warnings**: Language, Minors having Sex, Protected Sex, Unprotected Sex, Toys, Rimming, Oral Sex, Deep Throating, Frottage.

Disclaimer: I do not own How to Train Your Dragon. This is a piece of fiction and the author is making no monetary gain off its creation.

* * *

Berk was a product of the industrial age. Up until Haddock Industries was founded, the island had been unhabituated save for the occasional scouting units by international militant groups during wars. Haddock Industries had started as a one-man shop, selling in commodities across the globe. It had grown over the first decade into a chain of offices across five different countries, the main one being back at Berk. With its design came the employees, working across the spectrum from accounting to zoology. There wasn't a thing in the known world that didn't have Haddock's hand in it.

As the business grew and people came to settle on the island, with it came other businesses. Not one to be put out by its own workers, Haddock Industries created competition that always had better revenue. Some businesses knew when to just give the company a large share in order to survive. Toothless' father had been one of the smarter small businesses, providing to the local schools a meal plan to receive quarterly profit margins.

Students that attended the Private School, making into Third Year, were always offered placement at the Private University on the island where they would receive tutelage in their designated field with a job lined up upon graduation. Students across the globe fought to get into the university because the persons future was golden.

Along the coast, nestled amongst the expensive condominiums and beach homes was Haddock Towers, a glass castle on the horizon. It was a motel that had started with twelve rooms, made to house visiting VIPs for Haddock Inc. As the years grew and the corporation became a power holder, it had also grown in size. Ten floors, including three presidential apartments, it was a gem.

Toothless had never been in the building himself. Having been born and raised in Berk, his family had a nice home above his father's restaurant. Some of the students at the local Academy had parties in the lower rooms during breaks, but this break the place was surprisingly empty as many students opted to leave the island for high-end vacations.

Stepping through the wide glass doors leading into an open floor, Toothless gazed up at the spiraling floors above him. It seemed endless, the amount of architecture placed into this one building. On his left, the concierge desk seemed hard at work just as the front reception bustled at their computers, talking with men wearing expensive suits.

Feeling out of place in his faded blue jeans and loose shirt Toothless shifted towards the shadows and the elevator, pleased that his prostitute had already secured a room. The price was starting to make sense, especially since the overall coverage didn't even pay for one night as this place.

The glass elevators came with a shutter, the wide doors sliding open to release an array of businessmen from various countries. Once empty, Toothless stepped in, hitting the second floor button with ease. His heart hammered as he watched the elevator rise, faster than he thought imaginable. It was only a second before the doors swung open again for the next floor and Toothless fought the urge to let the sliding doors close just to ride the elevator up to the top floor.

_Room 227B_.

Verifying the number on his cellphone and comparing directions with the plaque in front of the elevators, Toothless started left, his sharp eyes looking over the railing at the wide reception area below him. A limousine had pulled up in front of the doors for the businessmen and Toothless watched as they climbed in one after another. _One day that'll be you in those suits._ He smiled before disappearing behind the wall leading to the line of rooms.

The room in question was a double, both sides with a "Do Not Disturb" Sign in place. While building up the courage to come today, Toothless had pictured everything that could have gone wrong, from the pimp being in the room ready to mug him or there being the most unattractive, disease-ridden prostitute.

He still came though, with high hopes that there would be a babe on the other side. _It's now or never._

With a deep breath, Toothless rapped his knuckles over the thick wood and stepped back. Inside he heard the slight scuffle of drawers being shut and the metal latch sliding open before the handle moved. The heavy oak pulled back an inside stood a decent sized young man, no older than fifteen. He had bright green eyes and the softest brown hair Toothless had ever seen.

"Um…" Toothless looked around. "Are you, um, the person I texted?"

"Looking for good time?" The boy tilted his head back, flashing pearly white teeth. Toothless nodded. "Good, come on in." The boy held the door open, giving the student room to come in. It wasn't lost on Toothless that the boy glanced around the hall before shutting the door, locking the chain once more. "Do you have the money?"

"Yeah." Toothless pulled out his wallet, taking out the folded bills with some despair. His bank account was certainly smaller now, but he kept reminding himself it was going to a good cause. He handed the cash over and watched as the prostitute counted the bills before dipping the money into his back pocket. He shifted nervously. "Look, I've, uh, never done this before."

"Got a whore?" The brunette inquired, unbuttoning his tight white shirt. Under, Toothless noted, was a tight band tee.

Face burning, Toothless nodded.

The boy pierced his lips, staring blankly at the wall. "It's easy. I'm yours until noon tomorrow. Pretty good bargain at that price, don't you think? No scarring, no scat – take a piss on me and I'll kill you. Follow those rules and we should be cool." He licked his dry lips before turning to Toothless again. "You can call me Hiccup. I hope you weren't expecting a woman."

"Um, Toothless." The student rubbed his head, unsure if the name he was given had been a codename. Berk-ian names were always so confusion. "And I'm cool, either way."

He nearly jumped out of his skin as Hiccup fell to his knees in front of him. The boy – Hiccup – was staring up at him with half lidded eyes, plagued with some annoyances. "Good, there were no refunds." His deft fingers pulled at Toothless' fly, unzipping it with haste. The dark haired teen nearly jumped from his skin as the cold hands wrapped around his soft – but definitely hardening – cock, pulling it free from his briefs and through the slit in his pants. _Oh gods, this is really happening._

Slumping against the nearest wall, Toothless let his hands fall back to avoid grabbing Hiccup's face and just getting him started. It seemed he wasn't the only one with some reservation about this meeting. For all his going nature, Hiccup appeared conflicted with where to go next, the paid of his thumb brushing the underside of Toothless' cock as his pink tongue stuck between his lips in thought. Finally after some conflict, Hiccup leaned forward and curled his tongue around the dark tip.

Toothless tilted his head back, exhaling heavily as a sharp twinge flooded his body. The next lick moved from the vein under his cock back towards the tip before he was enveloped in the warm heat of Hiccup's mouth. The boy's hands moved down, through the zipper of his pants, to grasps his balls, hanging heavily between his thighs. Eyes closed, Hiccup's face was moving closer to Toothless' body, taking in more and more of his cock. The slither of the tongue against the underside of his penis was indescribable. His own hand was nothing in comparison to the mouth, especially as the tip brushed against the back of Hiccup's throat.

_Spongy_ was his first thought, _Fuck yeah_ his second.

His fist tightened, uncertainty crossing his mind. The need to lace his fingers in that smooth hair, to push his dick in further, was unbearable. _If a mouth feels like this, just imagine being balls deep._ He groaned as Hiccup pulled back the smallest of moans. The warm breath flooding from his nose made Toothless shutter. Opening his eyes, he watched as Hiccup rolled forward again on the balls of his feet, swallowing Toothless down again. "Shit!" He felt his hips jerk forward. The throat around his tip tightened before Hiccup pulled back, coughing. "S, sorry…"

"Didn't get you, did I?" Hiccup asked, rubbing his jaw.

"No. Sorry, didn't mean to..."

"It's all right. Fuck my mouth." Hiccup's lips curled up. His hands left Toothless' jeans, grasping at Toothless' bigger ones, rougher ones, bringing them forward to rest on his jaw. Brushing his hands over Hiccup's low cheek bone, Toothless leaned forward, nearly arching over Hiccup as he pushed his hips past the plane of puffy lips. Hiccup's tongue rubbed against the underside of his cock again as he pushed against the back of the throat. As he touched the spongy part, he pulled back again, trying to tilt Hiccup's face just right. "You look good like this."

Hiccup's eyes sparkled, begging him to do it.

He pushed forward, easing his hips again into the spot He watched as Hiccup's cheeks hollowed out around him, creating a vacuum. Perfect didn't even cover the feeling he was having. In and out, he thrusts became greedy as he listened to the noises he was forcing from Hiccup. _Gug, gug, gug._ Hiccup had shifted himself around just right so he was on all four, his mouth parted and ready as Toothless kept him in place. Green eyes were dark with lust, staring up and watching Toothless.

"Shit… shit…" His orgasm was building. His balls were drawing in, belly coiling with each slap. He pulled back, fisting his shaft. The first line spilt against Hiccup's tongue and down his chin the second one creating a line over his nose as Toothless pulled the orgasm. Slumping back against the wall, Toothless watched as Hiccup pulled back, sliding his fingers down his face and through the mess.

And his lap… Toothless took a glance towards the tight designer jeans Hiccup was wearing, proudly defining his own erection. Taking even breaths, the student returned the smile. "I want you on the bed."

Hiccup stood on his knees, taking a cautious step towards the double bed. He leaned forward on the firm mattress, pressing his still-clothed ass out, accentuating his better features. Grinning, Toothless started forward. His open palm slapped Hiccup's back side causing the boy to shout before they slid down to the folds off his ass, grabbing. Leaning his mouth forward, Toothless licked the bare skin along Hiccup's collarbone where it disappeared under the tight black shirt. "Always was an ass man."

"No scars," Hiccup reminded him as his teeth grazed over the skin.

Pulling his mouth back, Toothless pressed the line of his body against Hiccup. Hands moving, he grasped at the button, freeing it and unzipping the tight pants from tiny hips. As if to help, Hiccup worked them hem line down. Counterintuitive to the process, he rolled his hips back. Toothless groaned, pulling his hips back and watched as the jeans slid down until Hiccup could toe them off. Grabbing his own hemline, Toothless discarded his pants, kicking them off towards the corner of the room with his underwear. Next, he pulled his shirt over his shoulders before letting it join his other clothes.

In an equal state of undress, Hiccup raised a knee onto the bed, sending a cool look over his shoulder. "Condoms," he purred, "Are in the side drawer."

"Don't need it yet." Toothless bent down, spreading Hiccup's white globes apart. There, deep in the middle was the boy's pink entrance, winking at him, offering so much on the other end. Just south, nestled between skinny thighs were the boy's testes, proportional to his size, and leading up to a small fat penis. Toothless ran his fingers down the line, from tailbone to perineum. No hair, he noted absently. A very well-maintained prostitute.

He had watched porn in preparation of tonight, not wanting to come in a complete and utter virgin. There was something about being humiliated for his experience he didn't want to relieve, especially when the mockery came from someone he was paying to help alleviate the situation. Hiccup had been good humored about the whole thing, offering the patience and goodwill, apparently used to the greediness of the client.

"You look so good," Whispered Toothless, purposely breathing against the pink orifice. Hiccup moaned, shifting again. His leg, settled net to Toothless' shoulder, stretched out to provide better view. Cupping his hands against the boy's globes, he spread the skin apart and curled his tongue against the rippled edges of the anus. It didn't taste like anything, he noted absently. Hiccup had certainly cleaned up well in preparation, but it was to be expected. He hadn't known if Hiccup was going to be a male or female and Hiccup certainly didn't know Toothless' sex prior to opening that door. _He prepared for anything_.

He kissed the skin next before bringing his tongue once more over the skin, pressing against the tight muscles blocking his path. Hiccup made a low, muffled sound as his hips shifted back again. Unabated, Toothless brought his thumb against the pink rim, pulling the taut skin back as his tongue once more slid against the velvety edges, the bright pink pulled white before disappearing into darkness. Nosing forward, the dark haired teen wedged his hands in the pull Hiccup's anus open until his tongue slipped firmly between the tight muscles. Saliva slipped from the corner of his mouth as he moved, licking the velvet deepness, enjoying the spicy scent of Hiccup's body wash.

He really was an ass man. Women's asses, men's asses. His screening of porn videos always included this and he had wanted to put his nose between those milky legs on the laptop screen. He wanted to bathe the back entrance with his own saliva and drive those mews forward

As his tongue stretched further in, he scrapped his front two teeth over the rolled up rim. Hiccup gave a startled his second leg sliding back to the ground as his hips shifted back, trying to push Toothless further in. Put his hands on Hiccup's hips, Toothless rolled his tongue out and down against Hiccup's perineum, collecting salty sweat before he moved once more up to the puffy, wet entrance. This time, his tongue was gobbled up greedily. Rolling his tongue, Toothless pulled out before sliding in again, an approving noise escaping his lips as Hiccup clenched his anus muscles.

The thin hips were rolling against the mattress under his palm, dry humping in desperate need. Hiccup's small voice, panting against satin fabric, begged hoarsely, "Please, I need you in me…"

"Let me get the condom." Toothless purposely stood and arched himself over Hiccup, letting his returned erection rub against the cleft of the boy's ass as he reached for the nightstand. True to his word, a box of condoms was in the drawer with a bottle of untouched lube. Forgoing the lube – he wasn't going to need to help masturbate now – Toothless tore open the box and ripped open one of the small aluminum packaging. It fit snug around him, leaving a wet mess on his hand as he unrolled it around his stiff cock.

This was it, Toothless rubbed the slick tip of his cock between the moist folds of Hiccup's bottom. Hiccup was watching him over his shoulder, eyes dark and bloodshot. He made someone need him – even though paid. Hiccup could have just rolled over and taken it, but that (Toothless was sure of it) was the face of a person who not only wanted, but needed Toothless to bring them off. Grabbing the base of his cock, he pushed forward, past the loosened ring of muscles.

Under him, Hiccup hissed. His grip on the bed spread tightened. Toothless placed his heavy hands on the boy's hips, stopping Hiccup from pulling away. Pushing a little further in, he groaned at the tightness around his dick. This, he realized, was far better than the other teen's throat had ever been. _No wonder everyone at school is doing it._

He couldn't wait. He bucked his hips forward and pushed the rest of his dick deep inside. Hiccup gave a startled cry, pulling on the blankets. Waiting, the older boy rubbed the bruises already forming on Hiccup's hips, waiting for the boy's breathing to thin out and the obvious pain to go away.

"P, please…" Hiccup whispered, pushing himself on his knees, "Please move."

Nodding, Toothless pulled his cock out until only the head remained pierced inside. Moving his leg around to better angle himself, he pushed forward once more until he was once more balls deep again. Hiccup groaned. Pulling the boy's hips back, Toothless tried again. In, out. Slowly a rhythm built up, the slapping of skin filling the room. It still didn't compare to the porn, Toothless realized as he pulled again, the orgasm building inside him.

_He should be begging for my cock. Why isn't he?_

Hiccup's head was ducked down, his breathing labored. Between his legs, his erection bobbed back and forth Toothless shifted his hips, trying for a different angle. Pushing his hips forward again, he heard a startled gasp from Hiccup. He pushed again into that very spot, pleased when Hiccup pushed back against him. Body rocking, Hiccup moaned and cried with each thrust. Tightening his grip on Hiccup's hips, the older teen dripped into that spot, relishing in the sounds of Hiccup's moans.

"More, fuck, oh gods…" One of Hiccup's hands moved, wrapping around his balls, attempting to ward off his own orgasm. Grabbing that hand, Toothless pressed it back against the bed moving his weight to push Hiccup down. His other hand moved to grab the brunette's free one, pressing both smooth, pale hands to the bed.

His hips worked fast, slamming into that very spot. His balls kept slapping against the warm flesh of his partner, loud to his ear. He wasn't going to last long, but it didn't seem right to come before his prostitute. "You feel so tight…" Hiccup did. Each thrust seemed to be wrapped in the warmest of gloves that convulsed around with a grip. It was becoming too much for him. His thrusts, once even, were erratic and sharp against that spot.

Head turned, Hiccup wiggled and cried, mouth parted and droll spilling on the comforter. "Oh gods, please…need to…oh fuck…so good…ah! Ah!" He back arched and buttocks tightened as he spilled between them.

The grip around his dick grew even hotter. Toothless tossed his head back as he spilt inside the condom, finally. He stayed still for a few seconds, a few tentative thrusts still in him, trying to imagine what he would have been like to be inside that tight spot surrounded not by latex, but by his own warm seed. Finally, he pulled free and pulled the condom off, tossing it in the waste basket found between the beds.

Sitting up, Toothless took in the mess of a prostitute he'd left under him. Hiccup, eyes closed and breathing heavy, was blanketed in a thin layer of sweat. His hips were red, forming black along the center where his hands hand tightened. There was scratching along the folds of his buttocks where Toothless had pulled the mounds apart and between them, puffy and red and slick with lube from the condom was Hiccup's anus, almost ready for another go.

Dipping his fingers in, Toothless felt a wave of joy go through him as Hiccup's back entrance swallowed his finger with no resistance. Face pressed against the blanket, Hiccup groaned. "I have you until noon."

Hiccup rolled his head to the side. "Mm. I have us on reserve for food as well."

"We'll have to see if we have time to eat." Toothless smirked, curling his fingers against a velvety spot that made Hiccup moan. "There's so much to do and I only have so much time to do it."


	3. Chapter 3

Saturday Night  
**By**: Selim  
**Rating**: M+  
**Summary**: Toothless has a problem – a big one. About to enter his last year of school, it occurs to him he's the only virgin in his class. In hopes to rectify that, he stumbled upon a number for a prostitute. One night is never so easy.  
**Pairing**: Human-Toothless/Slut?Hiccup  
**Warnings**: Language, Minors having Sex, Protected Sex, Unprotected Sex, Toys, Rimming, Oral Sex, Deep Throating, Frottage.

Disclaimer: I do not own How to Train Your Dragon. This is a piece of fiction and the author is making no monetary gain off its creation.

* * *

Toothless had always had trouble waking up in the morning. It was a complaint of his mother that had started when he began school. If he had it his way, he would have slept until noon or later. This, he decided with half-lidded eyes and brain fogged with the need to sleep more, was a good way to wake up in the morning.

Hiccup, it seemed, was very much a morning person. If Toothless had been the prostitute, he would have slept in until his costumer woke up, soaking in the free time doing nothing while his client slept away his paid time. Not Hiccup, apparently he was getting something out of the deal because he woke _Toothless_ by sliding his legs over Toothless' thighs and offering the most delightful show as his ass swallowed his protected cock.

God, what an ass. Blemished just right with the yellow markings of fingers over the course of the last couple hours, it was soft and loose, eager for another go. Toothless groaned and the skill both parties had built upon each other over the night. Hiccup, no longer guarded with his own pleasure and Toothless, no longer nervous about his prostitute's feelings. Both were greedy for the other, to fall victim to a whirlwind of pleasure that would end in just a few hours.

Cupping the red bottom displayed in front of him, Toothless tried to focus on the rise of his hips. His legs were stretched out in front of him as Hiccup bounced on the balls of his feet, knees bent and attention focused only on his own pleasure. Not that Toothless felt forgotten.

"Fuck, you're so slick…"

He had attempted to lube Hiccup better their second romp, fully in bed. He'd rubbed a few off on Hiccup as well, leaving a line of flaking come in its wake. There had been a few tryst that he hadn't bothered the penetrate, wanting to enjoy to sight of his cum spraying across the fucked over ass even though all he wanted to see was it sliding from Hiccup's puffy red hole.

Now it was dripping wet with the cooling lube Hiccup had supplied. Pink globes were crusted with dried semen, promising to be uncomfortable the longer Hiccup refrained from a shower, but clean was the last thing on their minds.

Grabbing Hiccup's thighs, Toothless pushed the pliant body back down, pushing his throbbing shaft deeper inside smooth insides. He could imagine his cock, bare, trying to nestle as deep as possible and blow a load, to mark this soul as his.

In, out, in…

The latex wrapped out his cock seemed to gleam each time it was pulled out, tugging on the thin muscles with it. Hiccups bottom came down again, swallowing more in before Toothless had had enough, swinging them both over, twisting Hiccup like a pig on a spit. Tugging Hiccup's legs apart, Toothless settled on his own knees, working his hips forward. This angle, he decided, was better – not only could he watch his dick mark the insides of the prostitute, but he could also see Hiccup's penis lay proudly against his stomach.

"Look at that little boy penis," Toothless jested, thrusting in. In response it bobbed up, knowing that it was the center of attention. "Not even a hair – did you shave it all off? I bet you did. Such a good little whore." He licked his dry lips, pushing Hiccup's legs back so the boy was bent in half. Fuck, he felt like he was in the boy's _stomach_ at this angle. It was so tight and deep, moist with lubricant. Almost like this spot was made for him.

Folded, Hiccup's hands reached behind him to grab the blanket, cheeks flushed and eyes closed. His red mouth was parted, lips chap. He looked like a debauched mess with no one to blame but the man currently plowing into him.

"Look at me," breathed Toothless.

Green eyes opened, staring up at him.

"You're such a good boy."

He brought a knee forward, seeking better balance as he raised Hiccup's hips. _Slap, slap, slap_, his rhythm was erratic, paced with his breathing. His eyes moved up to the perky nipples standing at attention. Just last night he had bit and sucked on them like a babe, enjoying the cries that left those swollen lips. Now they were bouncing up with each thrust, an enticing show.

"What do you want?" Toothless asked.

"Ngh," Hiccup blinked away the tears building in the corner of his eye. He tried opening his mouth again but a smaller moan escaped surrounded by breathing. Slowing his thrusts with sheer willpower, easing his dick free, he grasped the head of his cock to ease the urge to orgasm. With torturous precision he rubbed his cock against the greedy opening. "P-puh, please, Toothless."

"Tell me, Hiccup."

"N, need it, need your huge cock." Hiccup pushed his hips down, sliding Toothless' length over the folds of his butt. He groaned in defeat. "L, let me cum."

Shifting his hips back, Toothless eased his dick back in with the faintest of moans. Quickly he picked up his pace again, aiming directly into that spot. The muscles convulsed against him as Hiccup cried out with a startled cry.

"Ugh! Fuck! Uh-! Toothless!" Hiccup's grip tightened again on the blanket, pulling it up as he rocked back into the thrusts. "Ngh!"

"Huuh…hu'h…shit," Toothless clenched his jaw His orgasm, built up, was powerful. Hiccup cried out, tossing his head back as he painted his stomach with cum.

Pulling out, Toothless tossed the condom into the trash before slumping against Hiccup's side. Above his head, the alarm blared the bright red time of eight in the morning. "Gods, are you always up this early?"

"Early bird gets the worm."

Smirking into his pillow, Toothless breathed, "But the second mouse gets the cheese."

He grunted as an open hand slapped his hip. "I'm going to take a shower." Hiccup rolled out of bed, shifting with some discomfort before moving towards the door with an uneven gait. Toothless took in the sight with pride. _I did that to him._

As the water turned on, Toothless rolled out of bed and started towards the bathroom. _He didn't say I couldn't join him._

Hours later, dressed and fully sated, Toothless made his way back through town with a sense of dissatisfaction of what had transpired. Now over, it seemed almost painful to leave Hiccup. _Sex is really a dangerous game._ It was hard to remember that in the end, Hiccup was a prostitute. Nothing more, nothing less. It wasn't going to be easy to forget that special person after the night of passion the two had spent together.

His father's restaurant was closed on Sundays, used as a day when stock came in. It was quiet in the back room where his father sat at his computer, typing in the receipts from the week in the ledger. Knocking on the door, Toothless raised the corner of his lip when his father glanced up. The man always seemed tired on Sundays, but he made it worth it by taking Mondays and Tuesdays off.

"Your mother and I missed you last night."

"Yeah, there was this party and," Toothless trailed off absently.

"That's good," his father murmured, absently. He moved a sheet of paper, transaction sheets if Toothless recalled correctly. "Your mother and I worry sometimes that you forget how to be a kid." He made eye contact with his son finally over the rim of his glasses. "We're proud of you, Toothless, really we are, but you have to remember to slow down and smell the roses. These are the best years of your life and you should live them before they're gone."

"I know, Dad." He'd heard it all before from both parents. Ever since he'd been accepted at Berk Academy, years had been wasted with his nose in the book. Until Friday, he hadn't realized how isolated he was. "Did you have any problems at work?"

Chuckling, his father opened another ledger. "Contrary to belief, Toothless, I don't need you to run this place. I have a lot of capable young men able to help me do prep work and stock. The only advantage with you working is that I don't have to pay you hourly wages."

"I know, I know, you grace me with the right to breathe." Toothless smiled. "I'm going to go upstairs to get a shower, maybe take a little nap."

The older man glanced up again, a heavy brow raised in confusion. "It looks like you already had a shower."

Running his fingers through his wet hair, Toothless blushed as the memories flooded back. Hiccup had been so pretty pressed against the wall, water cascading down his abs as Toothless rubbed against him. Their semen spiraled together as it was washed down the drain. "It was a quick wash, one of the girl's was sick so, yeah, I just wanted to clean up a bit, but it's never feels like your shower."

"True. Go relax. Your mother is probably still sleeping; she had overnight rounds at the hospital so try not to wake her."

"Yes, sir."

"And if you could help tomorrow with the shop in the evening. Tinhead's wife has a doctor's appointment and he didn't want to miss out."

"Yes, sir."

Excusing himself, he moved out the backdoor, towards the winding staircase hidden in the alley that moved to the apartments up the stairs. It had been renovated when Toothless was still a child into a single-family home with full amenities, providing a comfortable living condition. The sounds and smells of the kitchens were canceled out upstairs, allowing the cool wisps of jasmine to circle Toothless as he walked into the nice earthly-tone walkway.

Shoes abandoned at the door, he moved through the open concept living room, up the staircase the entered an old loft where his rooms were located. A small bathroom and a bedroom next to a sanctioned off office. It was cozy, Toothless hummed as he carefully shut his door and moved through the single space.

Unlike his dorm room, it had a few more personal touches. Creamy walls were plastered with various posters, from favorite bands (outdated) to an old periodic table that had chemistry notes posted around it. His desk, in the corner, had books appropriately placed on it next to his old PC computer and printer. He'd left his coat from winter break on the back of the desk chair, catching dust.

The shower was exactly what he needed. He allowed the warm water to flow down his back, pleased with the lack of _need_ in his body. He doubted he could get an erection after the last twelve hours.

Hiccup had walked him down to the lobby at noon, politely thanking him for the good time and a reminder to keep his number if Toothless ever needed servicing again. The price, he had commented absently, was discounted at twenty percent off, but if Toothless wanted anything special (he didn't describe what would be special), the price would be back up in the two hundreds.

Then he had left, going back upstairs without another word.

The student in him wanted to get rated on his prowess, to learn what he needed to work on. There were still so many more conquests at school and he had to be prepared. He contemplating texting Hiccup to asks, but dismissed the thought just as quickly. Their services were through; he had no other reason to keep the number now that he was no longer a virgin.

Definitely not a virgin.

Turning off the shower, he stepped out.

Dressed in a fresh pair of boxers, Toothless laid out on his bed, nosing through his messages over the night. He had had an ignored message from his father telling him that the house was going to be locked overnight and where to find the spare key (coded 'you know where'). Meatlug had sent a message about his own conquests with his date ('score!') followed by a polite message to call him.

Hitting his friend's number, Toothless leaned back.

"Yo, man. Caught me just in time."

"Sorry, was out late last night." Toothless scratched his nose. "Figured you were too. You and Angelbite have a good night?"

"Up until my dad called telling me to get my ass home, which is why I needed to talk to you. I'm heading out for the week, surprise family vacation before The Interview. He's in high hopes that he's padded the pockets of the right people that I'll get in even with my abysmal grades, but hey – I'm not looking a gift horse in the mouth. This might be the last time I get to enjoy the beaches on his dime," laughed Meatlug heartily.

Toothless smiled. Meatlug had admitted their first year he had only attended the academy because his father had made him. He had wanted to attend the public school, to be with his girlfriend. He had the smarts to make it at the academy, but he was the kind of boy who had rather been a big fish in a small pond than matched with other piranhas. "He's going to kill you when you fail out of the Academy."

"Now failing, just going to do my bare minimum and then be the example of what not to be during an interview. He'll get over it; I mean I have four other siblings. Let him put his hopes and dreams in them for once." Meatlug snorted. "Anyway, where were you last night man, I had hoped we could get a bite before vacation really set in."

"Sorry, I was, uh, you know, with company." Toothless flushed.

"Your grandparents in town? The sucks."

"No! Uh, no. Not that kind of company," Toothless coughed. "I was with someone I had met. Spending the _night_." He emphasized the word, hoping his dearest friend would catch on.

Meatlug went silent. "I thought you weren't interested in you-know-what. Said it was a waste of time while we were in school."

He remembered saying that earlier that year when Meatlug had first had sex. If he remembered correctly, he had said he wasn't interested in any of the carnal pleasures while there was so much at stake. At the time, he had only to focus on being the best at school. Sex and fun could come after.

Oh how fast things had changed.

"I realized just how behind I really was," Toothless admitted.

"Oh well, congrats?" There was a cough on the other end of the line as Meatlug shifted the phone to his other ear. In the distance Toothless heard the sound of people talking at the airport. "When will I get to meet her?"

"Him." Toothless scratched his chin.

"Right, him. Didn't know you swung that way, but to each his own. Do I get to meet him? I mean, you've met Angel, so it's only fair."

Sighing, Toothless rubbed his eyes. "Probably not, it was a hookup at the party. They left their number and we met and got caught up. I think he gave me a codename to be honest." Not the full truth, but Meatlug did not need to know he'd spent his evening with hired service.

"That sucks. Maybe you'll meet them again, especially at your dad's place. Everyone comes to the Night Fury in Berk, so maybe you could catch up again and try to make something of it?"

"Maybe." Toothless highly doubted it. He'd never seen Hiccup before, even after years of working at his father's restaurant.

There was a loud buzz in the background as Meatlug attempted to cover up the speaker to argue with his father. "Hey, Toothless, I've got to go, our pilot just got in with the flight plan. I'll call you when I get back next Saturday. Try not to overwork over this week, cool?"

"Of course. You have fun, ride a wave for me."

"Ch. The only waves I'm riding better be on the beach. You haven't seen this fat ass in a swim suit. Not a pretty sight." Meatlug laughed. "I'll talk to you later."

"You too. Bye."

Hanging up, Toothless flung his arm behind his head, moaning as he relaxed into the softness of his own bed. Even though it was a twin size bed, it felt so big with just him in it, the missing warmth of a person next to him already noticeable. He exhaled heavily.

"Toothless, sweetie?"

Tilting his head to the side, he groaned at the heaviness of all his muscles. "'M upstairs, mama."

Within seconds, knuckles rapped at his door before the petite woman stepped in. Toothless' mother, Starfly, took a second to take in the space, ensuring that things were not out of place. She always made sure when he came back home things were just as they had been when he'd left. He loved that about her. "I wanted to check in on you, you didn't come home last night."

"Went to a party, mama."

"One of your school friends?" Toothless nodded. "That's nice; I was worried that you would leave school with just Meatlug. He's a nice boy, but growing souls need lots of support." Starfly settled on his bed, running her fingers through his hair. "Have you eaten yet?"

"Had a little something," Toothless murmured. "Just was woken really early this morning. Need at least twelve hours to function properly."

"So lazy, just like your father." She smiled. "Did you meet anybody at the party? Girls? Boys?"

Toothless grunted. "You've been sent up here to pry, haven't you?"

"A mother is allowed to have interest in her son's life. Especially at your age. We had already had Merryweather by then. I suppose as a parent, we worry that you would take things much too fast or much too slow. I want you to be happy. Tell me, are you happy?"

Toothless rolled on his side, grasping his mother's hand. "I was, for a second." And he had been, while lying in that hotel bed with Hiccup. It had all seemed right. "I did meet someone, spent all night with them." There, he said it.

His mother made a small noise. "I hope you used protection."

His cheeks flared.

"We've had the talk; or rather your father says you two did. Girls were so much easier at this stage. Keep your legs together, I told your sister. She seems happily engaged, but heaven knows if she listened to me. Society is so much crueler to the girls that sleep around than the boys. I just worry. You're so much like your father and, while I know you would make the right decision, I'm not ready to see you have a wife and children yet."

He grabbed his pillow, smothering himself. "I'm not talking about this with you."

Starfly laughed. "So, are we ever going to meet this person?"

Toothless groaned. Lying there for a moment longer he pulled the pillow free, meeting her concerned gaze. "Probably not. I… I really liked being with this person, but I still have so much to do and we aren't exactly the best match. Different aspirations, you know."

"Did you take the time to ask this person what they wanted to do?"

He had a feeling that it wasn't much, but his whispered anyway, "Not really."

"Then how do you know what they aspire to do with their lives. Maybe you should try to talk with them? I hear that does wonders."

"You mean meet with them again?"

"Did you get their phone number?"

Toothless nodded.

"Then give them a call, try to stay in contact with them. Maybe they made them happy too. You can't just let it fly past you. And remember, I raised you better than to be the boy who has flings with everyone. You're a wholesome young man."

"Yes, mama."

"I'm going to let you go back to bed. Try to be up by dinner. Your father rented that new elf movie and gods help me if I'm going to be tortured for three hours alone." She kissed his temple before stepping out of the room.

Blinking, Toothless pulled out his phone, gazing over his texts with Hiccup, two days ago. Still a number across his messaging screen, no name nor recognition. He thumbed his finger over the trash can on the side of the screen.

To delete or not to delete…

Twenty percent off Hiccup had said.

_Would you really pay just to see him again?_

His cock stirred to life, a reminder of how good the last twelve hours had been.

Thumbing his fingers over the message screen, he eyed Hiccup's contact info. The request was still blatantly there, but there was just something about it. Taking a deep breath, he pressed his thumb into Hiccup's phone number. _New contact, add contact…_

A rush of adrenaline flowed through him as he added Hiccup's number, on the just in case._Maybe one day,_ he hummed, _We can have one more night together._


End file.
